4-Chloro-6-methoxy-7-nitroquinazoline hydrochloride → 4-(2-Fluoro-5-methoxycarbonyloxy-4-methylanilino)-6-methoxy-7-nitroquinazoline hydrochloride

HRID 634743Notes

Reaction equation

HRID 634743 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([N+:15]([O-:17])=[O:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][N:4]=1.[F:18][C:19]1[CH:25]=[C:24]([CH3:26])[C:23]([O:27][C:28]([O:30][CH3:31])=[O:29])=[CH:22][C:20]=1[NH2:21]>C(O)(C)C>[ClH:2].[F:18][C:19]1[CH:25]=[C:24]([CH3:26])[C:23]([O:27][C:28]([O:30][CH3:31])=[O:29])=[CH:22][C:20]=1[NH:21][C:3]1[C:12]2[C:7](=[CH:8][C:9]([N+:15]([O-:17])=[O:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 212603064-Chloro-6-methoxy-7-nitroquinazoline hydrochlorideHCID 226250465-Amino-4-fluoro-2-methylphenyl Methoxyformate

Product 1

HCID 212603424-(2-Fluoro-5-methoxycarbonyloxy-4-methylanilino)-6-methoxy-7-nitroquinazoline hydrochlorideYield 91.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-6-methoxy-7-nitroquinazoline hydrochloride (784 mg, 2.8 mmol) and 2-fluoro-5-methoxycarbonyloxy-4-methylaniline (621 mg, 3.1 mmol), (prepared as described for the starting material in Example 26), in isopropanol (10 ml) was heated at reflux for 2 hours. The mixture was allowed to cool, the precipitated product collected by filtration, washed with isopropanol, ether and dried under vacuum to give 4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-6-methoxy-7-nitroquinazoline hydrochloride (1.12 g, 90%).

Workup

  1. custom(prepared
  2. temperaturewas heated
  3. temperatureat reflux for 2 hours
  4. temperatureto cool
  5. filtrationthe precipitated product collected by filtration
  6. washwashed with isopropanol, ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-6d95b8789c16449fb7234774c19c7ae2
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

Loading…